Pyridines and derivatives thereof as components for use in optoelectronic components

Abstract

The invention relates to an organic molecule comprising a structure of formula 1 and to the use thereof in optoelectronic components. wherein: X is SO2, CO or a C—C single bond; m is 0 or 1; n is 1, 2 or 3; r is 0 or 1; s is 0 or 1; LG is a divalent linker group, selected from: or LG is an element-element single bond.

The invention claimed is: 
     
       1. An optoelectronic device comprising:
 a substrate, 
 an anode and 
 a cathode, wherein the anode or the cathode is applied to the substrate, and at least one light-emitting layer is disposed between the anode and the cathode, wherein the light-emitting layer comprises at least one host material, wherein an activated singlet state (S 1 ) and/or an activated triplet state (T 1 ) of the at least one host material is higher than an activated singlet state (S 1 ) and/or activated triplet state (T 1 ) of the organic molecule, and wherein the light-emitting layer further comprises an organic molecule comprising a structure of formula 3b: 
 
       
         
           
           
               
               
           
         
       
       wherein: 
       m is 0 or 1; 
       n is 1, 2 or 3; 
       LG is a divalent linker group, selected from 
       
         
           
           
               
               
           
         
       
       or LG is an element-element single bond; 
       wherein AF2 comprises a structure of formula 2: 
       
         
           
           
               
               
           
         
       
       wherein: 
       x is 1; 
       y is 0; 
       o is 0 or 1; 
       p is 0 or 1; 
       A is CR*** when o=0, otherwise C; 
       VG1 is a bridging group and is selected from the group consisting of
 NR**, CR** 2 , O, S, a C—C single bond, BR**, AsR**, SiR** 2 , GeR** 2 , 
 
       
         
           
           
               
               
           
         
       
       when x=1 and at the same time y=0; 
       VG2=bridging group at each occurrence independently of one another is selected from the group consisting of CR** 2 , NR**, O, S and a C—C single bond, wherein two units VG2 are not equal to a C—C single bond at the same time; 
       E is NR**, 
       
         
           
           
               
               
           
         
       
       O or S; 
       G is C when o=1 and at the same time x=1; G is CR** when o=0 and at the same time x=1; 
       J is C when x=1; 
       L is CR*** when y=0; 
       R*** is R** or is selected from the following units, wherein a maximum of two of the radicals R*** are simultaneously one of the following units: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       R** at each occurrence independently of one another is a radical R* and/or marks the linking site to the linker group LG or in case m=0, to the pyridine unit of formula 3b; 
       R* at each occurrence independently of one another is selected from the group consisting of H, deuterium, phenyl, naphthyl, N(R 2 ) 2 —, —SCN, —NO 2 , a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 C atoms, each of which may be substituted with one or more radicals R 9 , wherein an adjacent CH 2  group may be replaced by —Si(R 4 ) 2 —, —Ge(R 4 ) 2 —, —Sn(R 4 ) 2 , —NR 2 —, —O—, or —S— and wherein one or more H atoms may be replaced by deuterium, F, Cl, Br, I, CF 3  or NO 2 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which in each case may be substituted with one or more radicals R 2 , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which with one or more radicals R 9 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which with one or more radicals R 9 , or a combination of these systems; 
       R 2  at each occurrence independently of one another is selected from the group consisting of H, deuterium, phenyl, naphthyl, CF 3 , a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 C atoms, each of which may be substituted with one or more radicals R 9 , wherein an adjacent CH 2  group is replaced by a —Si(R 4 ) 2 —, —Ge(R 4 ) 2 —, —Sn(R 4 ) 2 —NR 2 —, —O—, or —S— and wherein one or more H atoms may be replaced by deuterium, F, Cl, Br, I, CF 3  or NO 2 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which in each case may be substituted with one or more radicals R 9 , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted with one or more radicals R 9 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which with one or more radicals R 9 , or a combination of these systems; 
       R 4  at each occurrence independently of one another is selected from the group consisting of H, deuterium, phenyl, naphthyl, N(R 2 ) 2 , CF 3 , OH, a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 C atoms each of which may be substituted with one or more radicals R 9 , wherein or an adjacent CH 2  group may be replaced by —Si(R 4 ) 2 —, —Ge(R 4 ) 2 —, —Sn(R 4 ), —NR 2 —, —O—, or —S— and wherein one or more H atoms may be replaced by deuterium, F, Cl, Br, I, CF3 or NO2, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which in each case may be substituted with one or more radicals R 8 , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted with one or more radicals R 9 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which may be substituted with one or more radicals R 9 , or a combination of these systems; 
       R 8  at each occurrence independently of one another is selected from the group consisting of H, deuterium, phenyl, naphthyl, F, CF 3  or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical with 1 to 20 C atoms, in which also one or more H atoms may be replaced by F or CF 3 ; 
       R 9  at each occurrence independently of one another is selected from the group consisting of H, deuterium, phenyl, naphthyl, N(R 2 ) 2 —, CF 3 , NO 2 , a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 C atoms, each of which may be substituted with one or more radicals R 8 , wherein an adjacent CH 2  group may be replaced by —Si(R 4 ) 2 —, —Ge(R 4 ) 2 —, —Sn(R 4 ) 2 —NR 2 —, —O—, or —S— and wherein one or more H atoms may be replaced by deuterium, F, Cl, Br, I, CF 3  or NO 2 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which in each case may be substituted with one or more radicals R 8 , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted with one or more radicals R 3 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which may be substituted with one or more radicals R 8 , or a combination of these systems. 
     
     
       2. The optoelectronic device according to  claim 1 , comprising at least one host material comprising the organic molecule. 
     
     
       3. The optoelectronic device according to  claim 1 , wherein the light-emitting layer comprises one or more of a fluorescent material or a phosphorescent material and wherein the fluorescent material or the phosphorescent material are an organic molecule. 
     
     
       4. The optoelectronic device according to  claim 3 , in which the organic molecule together with a functional material forms an exciplex. 
     
     
       5. An optoelectronic device comprising:
 a substrate, 
 an anode and 
 a cathode, wherein the anode or the cathode is applied to the substrate, and at least one light-emitting layer is disposed between the anode and the cathode, wherein the light-emitting layer comprises one or more of a fluorescent material or a phosphorescent material and wherein the fluorescent material or the phosphorescent material are an organic molecule, and wherein the light-emitting layer further comprises an organic molecule comprising a structure of formula 3b: 
 
       
         
           
           
               
               
           
         
         wherein: 
         m is 0 or 1; 
         n is 1, 2 or 3; 
         LG is a divalent linker group, selected from 
       
       
         
           
           
               
               
           
         
       
       or LG is an element-element single bond; 
       wherein AF2 comprises a structure of formula 2: 
       
         
           
           
               
               
           
         
       
       wherein: 
       x is 1; 
       y is 0; 
       o is 0 or 1; 
       p is 0 or 1; 
       A is CR*** when o=0, otherwise C; 
       VG1 is a bridging group and is selected from the group consisting of
 NR**, CR** 2 , O, S, a C—C single bond, BR**, AsR**, SiR** 2 , GeR** 2 , 
 
       
         
           
           
               
               
           
         
       
       when x=1 and at the same time y=0; 
       VG2=bridging group at each occurrence independently of one another is selected from the group consisting of CR**, NR**, O, S and a C—C single bond, wherein two units VG2 are not equal to a C—C single bond at the same time; 
       E is NR**, 
       
         
           
           
               
               
           
         
       
       O or S: 
       G is C when o=1 and at the same time x=1; G is CR** when o=0 and at the same time x=1; 
       J is C when x=1; 
       L is CR*** when y=0;
 R*** is R** or is selected from the following units, wherein a maximum of two of the radicals 
 R*** are simultaneously one of the following units: 
 
       
         
           
           
               
               
           
         
       
       R** at each occurrence independently of one another is a radical R* and/or marks the linking site to the linker group LG or in case m=0, to the pyridine unit of formula 3b; 
       R* at each occurrence independently of one another is selected from the group consisting of H, deuterium, phenyl, naphthyl, N(R 2 ) 2 , —SCN, —CF 3 , —NO 2 , a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 C atoms, each of which may be substituted with one or more radicals R 9 , wherein an adjacent CH 2  group may be replaced by —Si(R 4 ) 2 —, —Ge(R 4 ) 2 —, —Sn(R 4 ), —O—, or —S— and wherein one or more H atoms may be replaced by deuterium, F, Cl, Br, I, CF 3  or NO 2 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which in each case may be substituted with one or more radicals R 2 , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which with one or more radicals R 9 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which with one or more radicals R 9 , or a combination of these systems; 
       R 2  at each occurrence independently of one another is selected from the group consisting of H, deuterium, phenyl, naphthyl, CF 3 , a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 C atoms, each of which may be substituted with one or more radicals R 9 , wherein an adjacent CH 2  group is replaced by a —Si(R 4 ) 2 —, —Ge(R 4 ) 2 —, —Sn(R 4 ) 2 —NR 2 —, —O—, or —S— and wherein one or more H atoms may be replaced by deuterium, F, Cl, Br, I, CF 3  or NO 2 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which in each case may be substituted with one or more radicals R 9 , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted with one or more radicals R 9 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which with one or more radicals R 9 , or a combination of these systems; 
       R 4  at each occurrence independently of one another is selected from the group consisting of H, deuterium, phenyl, naphthyl, N(R 2 ) 2 , CF 3 , OH, a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 C atoms each of which may be substituted with one or more radicals R 9 , wherein or an adjacent CH 2  group may be replaced by —Si(R 4 ) 2 —, —Ge(R 4 ) 2 —, —Sn(R 4 ), —NR 2 —, —O—, or —S— and wherein one or more H atoms may be replaced by deuterium, F, Cl, Br, I, CF 3  or NO 2 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which in each case may be substituted with one or more radicals R 8 , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted with one or more radicals R 9 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which may be substituted with one or more radicals R 9 , or a combination of these systems; 
       R 8  at each occurrence independently of one another is selected from the group consisting of H, deuterium, phenyl, naphthyl, F, CF 3  or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical with 1 to 20 C atoms, in which also one or more H atoms may be replaced by F or CF 3 ; 
       R 9  at each occurrence independently of one another is selected from the group consisting of H, deuterium, phenyl, naphthyl, N(R 2 ) 2 , CF 3 , NO 2 , a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 C atoms, each of which may be substituted with one or more radicals R 8 , wherein an adjacent CH 2  group may be replaced by —Si(R 4 ) 2 —, —Ge(R 4 ) 2 —, —Sn(R 4 ) 2 —NR 2 —, —O—, or —S— and wherein one or more H atoms may be replaced by deuterium, F, Cl, Br, I, CF 3  or NO 2 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which in each case may be substituted with one or more radicals R 8 , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted with one or more radicals R 3 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which may be substituted with one or more radicals R 8 , or a combination of these systems, wherein the organic molecule is a charge transport layer. 
     
     
       6. The optoelectronic component device according to  claim 1 , wherein in the organic molecule m is 0. 
     
     
       7. The optoelectronic component device according to  claim 1 , wherein the organic molecule comprises one of the structures 3.1, 3.2, 3.5, 3.6, 3.11 or 3.12, wherein optionally all C sp2 —H groups may also be C sp2 —R* groups and otherwise the definitions given in  claim 1  apply: 
       
         
           
           
               
               
           
         
       
     
     
       8. The optoelectronic component device according to  claim 1 , wherein in the organic molecule at least one chemically substitutable position comprises at least one radical R, wherein:
 R at each occurrence independently of one another is selected from the group consisting of H, deuterium, phenyl, naphthyl, F, Cl, Br, I, N(R 2 ) 2 , —SCN, —CF 3 , —NO 2 , —OH, a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 C atoms, each of which may be substituted with one or more radicals R 9 , wherein an adjacent CH 2  group may be replaced by —Si(R 4 ) 2 —, —Ge(R 4 ) 2 —, —Sn(R 4 ) 2 —NR 2 —, —O—, or —S— and wherein one or more H atoms may be replaced by deuterium, F, Cl, Br, I, CF 3  or NO 2 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which in each case may be substituted with one or more radicals R 2 , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted with one or more radicals R 9 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which may be substituted with one or more radicals R 9 , or a combination of these systems; wherein R 2  to R 9  have the aforestated meanings. 
 
     
     
       9. The optoelectronic device according to  claim 1 , wherein the organic molecule is one or more of a luminescent emitter, a host material, an electron transport material, a hole injection material and a hole blocking material in the optoelectronic component. 
     
     
       10. The optoelectronic device according to  claim 1 , wherein the optoelectronic device is an organic light-emitting diode, a light-emitting electrochemical cell, an organic light-emitting sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, and an organic laser or a down-conversion element. 
     
     
       11. The optoelectronic device according to  claim 1 , wherein the proportion of the organic molecule in the emitter is in the range of 1% to 99%. 
     
     
       12. The optoelectronic device according to  claim 1 , wherein the proportion of the organic molecule in the emitter is in the range of 5% to 80%. 
     
     
       13. The optoelectronic component device according to  claim 5 , wherein in the organic molecule m is 0. 
     
     
       14. The optoelectronic component device according to  claim 5 , wherein the organic molecule comprises one of the structures 3.1, 3.2, 3.5, 3.6, 3.11 or 3.12, wherein optionally all C sp2 —H groups may also be C sp2 —R* groups and otherwise the definitions given in  claim 5  apply: 
       
         
           
           
               
               
           
         
       
     
     
       15. The optoelectronic component device according to  claim 5 , wherein in the organic molecule at least one chemically substitutable position comprises at least one radical R, wherein:
 R at each occurrence independently of one another is selected from the group consisting of H, deuterium, phenyl, naphthyl, F, Cl, Br, I, N(R 2 ) 2 , —SCN, —CF 3 , —NO 2 , —OH, a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 C atoms, each of which may be substituted with one or more radicals R 9 , wherein an adjacent CH 2  group may be replaced by —Si(R 4 ) 2 —, —Ge(R 4 ) 2 —, —Sn(R 4 ) 2 —NR 2 —, —O—, or —S— and wherein one or more H atoms may be replaced by deuterium, F, Cl, Br, I, CF 3  or NO 2 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which in each case may be substituted with one or more radicals R 2 , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted with one or more radicals R 9 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which may be substituted with one or more radicals R 9 , or a combination of these systems; wherein R 2  to R 9  have the aforestated meanings.